Cesium carbonate → 1-[(2-Hydroxy-1,2-dimethylpropyl)amino]-7-(pyridin-3-ylethynyl)-5H-pyrido[4,3-b]indole-4-carboxamide

HRID 1971005Notes

Reaction equation

NC1N=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[C:12]4[C:20]([NH:21][CH:22]([CH:26]5[CH2:28][CH2:27]5)[CH:23]5CC5)=[N:19][CH:18]=[C:17]([C:29]([NH2:31])=[O:30])[C:13]=4[NH:14][C:15]=3[CH:16]=2)=CN=1.C([C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=1)#C.C(=O)([O-])[O-:41].[Cs+].[Cs+]>CS(C)=O.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl>[OH:41][C:26]([CH3:27])([CH3:28])[CH:22]([NH:21][C:20]1[C:12]2[C:11]3[CH:10]=[CH:9][C:8]([C:5]#[C:6][C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)=[CH:16][C:15]=3[NH:14][C:13]=2[C:17]([C:29]([NH2:31])=[O:30])=[CH:18][N:19]=1)[CH3:23]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 1-[(2-hydroxy-1,2-dimethylpropyl)amino]-7-iodo-5H-pyrido[4,3-b]indole-4-carboxamide (prepared according to Examples 11 and 35, 50 mg, 0.11 mmol), 3-ethynylpyridine (18 mg, 0.17 mmol), cesium carbonate (74 mg, 0.23 mmol), and dichlorobis(tricyclohexylphosphine)palladium(II) (8.4 mg, 0.011 mmol) in DMSO (1.1 mL) was purged with nitrogen for 5 min, heated to 120° C. for 12 h, cooled to room temperature, diluted with EtOAc, and washed with water and brine. The organic layer was dried, concentrated, and purified by flash chromatography to afford the title compound. LRMS (APCI) calc'd for (C24H23N5O2) [M+H]+, 414.2. found 414.1.

Workup

customwas purged with nitrogen for 5 min
temperaturecooled to room temperature
additiondiluted with EtOAc
washwashed with water and brine
customThe organic layer was dried
concentrationconcentrated
custompurified by flash chromatography

Sources & evidence

ORD record: ord-b04af4faafd74652952395a5df041756
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431569B2

Reaction notes

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