Potassium Carbonate → 2-(6-Chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester

HRID 2234064Notes

Reaction equation

HRID 2234064 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][CH3:9])=[C:4](I)[CH:3]=1.[C:11]([O:15][C:16]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1B(O)O)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:11]([O:15][C:16]([N:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[C:19]1[C:4]1[CH:3]=[C:2]([Cl:1])[N:7]=[N:6][C:5]=1[O:8][CH3:9])=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 230924816-Chloro-4-iodo-3-methoxypyridazine

Product 1

HCID 866120482-(6-Chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Argon is passed for 30 min through a suspension of 135 mg 6-chloro-4-iodo-3-methoxy-pyridazine, 130.5 mg 1-(tert-butoxycarbonyl)indole-2-boronic acid, 152 mg potassium carbonate, and 52.5 mg triphenylphosphine in 2.2 ml DME and 1.1 ml water. 11.2 mg palladium (II) acetate is added and the mixture stirred under reflux for 3 h. The product is isolated by extraction with ethyl acetate and purified by chromatography on silica gel yielding 80 mg 2-(6-chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester

Workup

  1. temperatureunder reflux for 3 h
  2. custompurified by chromatography on silica gel yielding 80 mg 2-(6-chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester

Sources & evidence

ORD record
ord-c4f482a9767e4c02a5124f717a16c35b
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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