Water → HCID 66835418, compound

HRID 536284Notes

Reaction equation

HRID 536284 reaction equation
Cl[C:2]1[CH:10]=[CH:9][N:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:11]([O:13][CH3:14])=[O:12])[NH:6]2.OB(C)[C:17]1[CH:18]=[C:19]([CH:27]=[CH:28][CH:29]=1)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:23]([O:22][C:20]([C:19]1[CH:18]=[C:17]([C:2]2[CH:10]=[CH:9][N:8]=[C:7]3[NH:6][C:5]([C:11]([O:13][CH3:14])=[O:12])=[CH:4][C:3]=23)[CH:29]=[CH:28][CH:27]=1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 37818556Methyl 4-chloro-1H-pyrrolo[2,3-b]pyridine-2-carboxylateHCID 66835407HCID 66835407, compound

Product 1

HCID 66835418HCID 66835418, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

A stirred slurry of methyl 4-chloro-7-azaindole-2-carboxylate (100 mg, 0.48 mmol), tert-butyl 3-(hydroxy(methyl)boryl)benzoate (137 mg, 0.62 mmol), potassium phosphate (309 mg, 1.42 mmol), tetrakis(triphenylphosphine) palladium (28 mg, 0.02 mmol) in p-dioxane (3 mL)/water (1 mL) were heated at 100° C. for 15 hr. The reaction mixture was cooled, concentrated in vacuo and flash chromatographed (0-100% ethyl acetate:heptanes) to afford methyl 4-(3-(tert-butoxycarbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate as a white powder (148 mg). 1H NMR (400 MHz, CHLOROFORM-d) d ppm 1.62 (s, 9H) 3.99 (s, 3H) 7.28 (d, J=5.23 Hz, 1H) 7.36 (d, J=2.62 Hz, 1H) 7.59 (t, 1H) 7.90 (d, 1H) 8.09 (d, 1H) 8.35 (t, 1H) 8.64 (d, J=4.70 Hz, 1H); m/z (M+1)=353.2.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated in vacuo and flash
  3. customchromatographed (0-100% ethyl acetate:heptanes)

Sources & evidence

ORD record
ord-861f03725ad24ca99c65a1605c87323e
Source dataset
uspto-grants-2014_10
Patent number
US08859577B2

Reaction notes

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