Water → HCID 118072730, compound

HRID 626406Notes

Reaction equation

HRID 626406 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]([C:15]2[CH:39]=[CH:38][C:18]3[N:19]([CH2:22][C:23]4[CH:28]=[CH:27][C:26](B5OC(C)(C)C(C)(C)O5)=[CH:25][CH:24]=4)[CH:20]=[N:21][C:17]=3[CH:16]=2)=[O:14])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].Br[C:41]1[C:42]([C:47]([O:49][CH3:50])=[O:48])=[N:43][CH:44]=[CH:45][CH:46]=1.C([O-])([O-])=O.[Na+].[Na+].O>COCCOC.C1COCC1.O.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>[CH:1]([C:4]1[CH:5]=[C:6]([C@@H:10]([NH:12][C:13]([C:15]2[CH:39]=[CH:38][C:18]3[N:19]([CH2:22][C:23]4[CH:24]=[CH:25][C:26]([C:41]5[C:42]([C:47]([O:49][CH3:50])=[O:48])=[N:43][CH:44]=[CH:45][CH:46]=5)=[CH:27][CH:28]=4)[CH:20]=[N:21][C:17]=3[CH:16]=2)=[O:14])[CH3:11])[CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 12828946Methyl 3-bromo-2-pyridinecarboxylateHCID 123521060HCID 123521060, compound

Product 1

HCID 118072730HCID 118072730, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 69365232HCID 69365232, compoundSolvent

Conditions

Temperature
100 °C

Procedure

The mixture of (S)—N-(1-(3-isopropylphenyl)ethyl)-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-1H-benzo[d]imidazole-5-carboxamide (94 ma, 0.18 mmol), methyl 3-bromopicolinate (20 mg, 0.09 mmol), Pd(PPh3)4 (11 mg, 0.009 mmol) and Na2CO3 (19 mg, 0.18 mmol) in DME/THF/H2O (2.5 mL/1 mL/1 mL) was heated to 100° C. and stirred for 18 hrs under N2. Then the mixture was poured into 10 mL of water, and extracted with EtOAc (10 mL×3), the combined organic layers was washed with water (10 mL) and brine (10 mL) and dried with Na2SO4. After filtration, the filtrate was concentrated under the reduced pressure. The residue was purified with prep-TLC (DCM/Methanol=20/1, silica gel) to give the titled compound.

Workup

  1. extractionextracted with EtOAc (10 mL×3)
  2. washthe combined organic layers was washed with water (10 mL) and brine (10 mL)
  3. dry with materialdried with Na2SO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under the reduced pressure
  6. customThe residue was purified with prep-TLC (DCM/Methanol=20/1, silica gel)

Sources & evidence

ORD record
ord-0f63e34185554f738d3595b364ffc709
Source dataset
uspto-grants-2016_04
Patent number
US09309227B2

Reaction notes

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