Dichloromethane → 2,2-dimethyl-propionic acid 5-(4-amino-3-dimethylcarbamoyl-phenyl)-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

HRID 2234670Notes

Reaction equation

HRID 2234670 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:12]([CH2:16][CH3:17])[N:13]=[CH:14][CH:15]=3)=[CH:9][N:8]([CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2=[N:6][CH:7]=1.[NH2:26][C:27]1[CH:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][C:28]=1[C:29]([N:31]([CH3:33])[CH3:32])=[O:30].ClCCl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C(#N)C>[NH2:26][C:27]1[CH:37]=[CH:36][C:35]([C:2]2[CH:3]=[C:4]3[C:10]([C:11]4[N:12]([CH2:16][CH3:17])[N:13]=[CH:14][CH:15]=4)=[CH:9][N:8]([CH2:18][O:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:5]3=[N:6][CH:7]=2)=[CH:34][C:28]=1[C:29](=[O:30])[N:31]([CH3:32])[CH3:33]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 574162382-amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 577314872,2-dimethyl-propionic acid 5-bromo-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

Product 1

HCID 577315452,2-dimethyl-propionic acid 5-(4-amino-3-dimethylcarbamoyl-phenyl)-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

2,2-dimethyl-propionic acid 5-bromo-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester, 2-amino-N,N-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzamide, [1,1′-bis(diphenylphosphino)-ferrocene]dichloro-palladium(II) complex with dichloromethane, acetonitrile, 1M aqueous sodium carbonate solution, and tetrahydrofuran were combined in a microwave vial. The tube was placed in a microwave reactor and irradiated to 120° C. for 20 minutes. The reaction mixture was concentrated in vacuo and the residue partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (0 to 100% [10% methanol in ethyl acetate] in hexanes) to give 2,2-dimethyl-propionic acid 5-(4-amino-3-dimethylcarbamoyl-phenyl)-3-(2-ethyl-2H-pyrazol-3-yl)-pyrrolo[2,3-b]pyridin-1-ylmethyl ester. MS: m/z 489.3 (M+H+).

Workup

  1. customThe tube was placed in a microwave reactor
  2. customirradiated to 120° C. for 20 minutes
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between dichloromethane and water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography (0 to 100% [10% methanol in ethyl acetate] in hexanes)

Sources & evidence

ORD record
ord-63f2728b39f64a5d96dcce30a8a8832e
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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