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

HRID 733731Notes

Reaction equation

HRID 733731 reaction equation
[Cl:1][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.[Cl: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>[ClH:1].[Cl:20][C:21]1[CH:27]=[C:26]([C:28]([F:30])([F:31])[F:29])[CH:25]=[CH:24][C:22]=1[NH:23][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

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 1620012-Chloro-4-trifluoromethylanilineHCID 578410404-Chloro-1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 68866665N-[2-Chloro-4-(trifluoromethyl)phenyl]-1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridin-4-amine hydrochlorideYield 37.7%

Reagents, catalysts & solvents 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)Catalyst2×HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-chloro-1-methyl-7-(4-morpholinylcarbonyl)-1H-pyrrolo[3,2-c]pyridine (100 mg), 2-chloro-4-trifluoromethylaniline (80 mg), cesium carbonate (168 mg), tris(dibenzylideneacetone)dipalladium (0) (3.4 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (2.3 mg) in 1,4-dioxan (2 ml) was heated to 100° C. under nitrogen for 2 h. Added tris(dibenzylideneacetone)dipalladium (0) (10 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (7 mg) and continued heating at 100° C. under nitrogen over night. The reaction mixture was diluted with dichloromethane and washed with water 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 (64 mg).

Workup

  1. washwashed with water
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification and salt formation

Sources & evidence

ORD record
ord-f302a0317986461491a91732e73d56a1
Source dataset
uspto-grants-2009_09
Patent number
US07589206B2

Reaction notes

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