Sodium Carbonate → HCID 66605878, compound

HRID 2410928Notes

Reaction equation

HRID 2410928 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:21]([NH2:23])=[O:22])[C:5]2[NH:6][C:7]3[CH:8]=[C:9]([N:15]4[CH2:20][CH2:19][O:18][CH2:17][CH2:16]4)[CH:10]=[CH:11][C:12]=3[C:13]=2[N:14]=1.[CH3:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[N:29][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.COCCOC>[CH3:24][C:25]1[CH:26]=[C:27]([C:2]2[CH:3]=[C:4]([C:21]([NH2:23])=[O:22])[C:5]3[NH:6][C:7]4[CH:8]=[C:9]([N:15]5[CH2:20][CH2:19][O:18][CH2:17][CH2:16]5)[CH:10]=[CH:11][C:12]=4[C:13]=3[N:14]=2)[CH:28]=[N:29][CH:30]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27627085-Methylpyridine-3-boronic acidHCID 86663061HCID 86663061, compound

Product 1

HCID 66605878HCID 66605878, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

2-Bromo-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxamide 325D (100 mg, 0.267 mmol), 5-methylpyridin-3-ylboronic acid (51.1 mg, 0.373 mmol), PdCl2(dppf)-CH2Cl2 adduct (10.88 mg, 0.013 mmol), and Na2CO3 (2M) (0.666 mL, 1.333 mmol) were mixed with DME (4 mL) in a sealed microwave vial. The mixture was flushed with N2 and heated at 110° C. in microwave for 1 hr. The mixture was filtered and then purified using preparative HPLC to give titled product. MS (ESI) m/z 387.97 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.33 (s, 1H), 9.25 (s, 1H), 8.52 (s, 1H), 8.44 (s, 1H), 8.43 (s, 1H), 8.36 (s, 1H), 8.09 (d, 1H, J=8.6), 7.87 (s, 1H), 7.23 (s, 1H), 7.03 (dd, 1H, J=8.9, 2.1), 3.81 (m, 4H), 3.25 (m, 4H), 2.44(s, 3H).

Workup

  1. customThe mixture was flushed with N2
  2. filtrationThe mixture was filtered
  3. custompurified

Sources & evidence

ORD record
ord-f55fc5b34b634c44805114a0011caf03
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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