Cesium carbonate → 1-Methyl-N-[2-methyl-4-(trifluoromethyl)phenyl]-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine

HRID 733729Notes

Reaction equation

Cl[C:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH3:11])[C:6]=2[C:5]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])=[CH:4][N:3]=1.[CH3:20][C:21]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:22]=1[NH2:23].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.ClCCl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>[CH3:11][N:10]1[C:6]2[C:5]([C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[O:13])=[CH:4][N:3]=[C:2]([NH:23][C:22]3[CH:24]=[CH:25][C:26]([C:28]([F:29])([F:30])[F:31])=[CH:27][C:21]=3[CH3:20])[C:7]=2[CH:8]=[CH:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-chloro-1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine (100 mg), 2-methyl-4-trifluoromethylaniline (60 μl), cesium carbonate (163 mg), tris(dibenzylideneacetone)dipalladium (0) (7 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (5 mg) in 1,4-dioxan (2 ml) was heated to 100° C. under argon overnight. The reaction mixture was diluted with dichloromethane and washed with water followed by saturated sodium chloride solution, then dried (MgSO4), filtered and evaporated. Purification and salt formation was as described in Example 101 to afford the title compound as a white solid (52 mg).

Workup

washwashed with water
dry with materialdried (MgSO4)
filtrationfiltered
customevaporated
customPurification and salt formation

Sources & evidence

ORD record: ord-1d84c94010124a2e823a584a3d911e90
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589206B2

Reaction notes

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