1,2-Dimethoxyethane → HCID 178433967, compound

HRID 1519788Notes

Reaction equation

HRID 1519788 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[S:13][CH:14]=[C:15]([CH3:23])[C:16]=2[C:17]2[NH:21][C:20]([CH3:22])=[N:19][N:18]=2)=[O:10])=[CH:4][CH:3]=1.[N:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)(O)[O-].[Na+].COCCOC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:23][C:15]1[C:16]([C:17]2[NH:21][C:20]([CH3:22])=[N:19][N:18]=2)=[C:12]([NH:11][C:9](=[O:10])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([C:27]3[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=3)=[CH:3][CH:4]=2)[S:13][CH:14]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 178433968HCID 178433968, compound

Product 1

HCID 178433967HCID 178433967, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A 30 mL reaction vial was charged with 2-(4-iodophenyl)-N-(4-methyl-3-(5-methyl-4H-1,2,4-triazol-3-yl)thiophen-2-yl)acetamide (140 mg, 0.32 mmol), pyridin-4-ylboronic acid (60 mg, 0.48 mmol), sodium bicarbonate (100 mg, 1.2 mmol), DME (2 mL), and water (2 mL). The heterogeneous mixture was stirred vigorously under a stream of nitrogen for 5 minutes before Pd(PPh3)4 was added and the vial was sealed under its Teflon cap. The reaction mixture was heated to 90° C. for 3.25 h before being transferred to a microwave vial and being microwaved to 150° C. for 5 minutes. The reaction mix was concentrated under reduced pressure and the residue was partitioned between methylene chloride and a saturated aqueous solution of ammonium chloride. The organic solution was washed with brine and dried over sodium sulfate. The solution was concentrated under reduced pressure and the crude product was purified by column chromatography (3.5% MeOH/methylene chloride) Yield: 10.0 mg (8%). Method [1]: rt=1.136 min; MH+ 390.2. 1H-NMR (300 MHz, CD3OD) δ 8.71 (d, J=6.3 Hz, 1H), 8.60 (dd, J=4.6, 1.6 Hz, 2H), 7.84 (d, J=8.0 Hz, 2H), 7.77 (dd, J=4.6, 1.6 Hz, 2H), 7.57 (d, J=8.2 Hz, 2H), 6.58 (s, 1H), 3.94 (s, 2H), 2.45 (s, 3H), 2.31 (s, 3H).

Workup

  1. customA 30 mL reaction
  2. additionwas added
  3. customcap
  4. custombeing microwaved to 150° C. for 5 minutes
  5. additionThe reaction mix
  6. concentrationwas concentrated under reduced pressure
  7. customthe residue was partitioned between methylene chloride
  8. washThe organic solution was washed with brine
  9. dry with materialdried over sodium sulfate
  10. concentrationThe solution was concentrated under reduced pressure
  11. customthe crude product was purified by column chromatography (3.5% MeOH/methylene chloride) Yield: 10.0 mg (8%)
  12. customrt=1.136 min

Sources & evidence

ORD record
ord-e23432ec6e2f412c9e77c699e5af4c4a
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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