Cesium carbonate → (4aS,9bR)-8-(2-cyano-pyridin-3-ylamino)-5-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole-6-carbonitrile

HRID 2215920Notes

Reaction equation

HRID 2215920 reaction equation
CN1C2C(C(F)(F)F)=CC(NC3C=NC=CC=3)=CC=2C2CNCCC12.C(OC([N:33]1[CH2:51][CH2:50][C@@H:36]2[N:37]([C:47](O)=O)[C:38]3[C:39]([C:45]#[N:46])=[CH:40][C:41]([NH2:44])=[CH:42][C:43]=3[C@@H:35]2[CH2:34]1)=O)(C)(C)C.Br[C:53]1[C:54]([C:59]#[N:60])=[N:55][CH:56]=[CH:57][CH:58]=1.C([O-])([O-])=O.[Cs+].[Cs+]>>[C:59]([C:54]1[C:53]([NH:44][C:41]2[CH:42]=[C:43]3[C:38](=[C:39]([C:45]#[N:46])[CH:40]=2)[N:37]([CH3:47])[C@H:36]2[CH2:50][CH2:51][NH:33][CH2:34][C@@H:35]32)=[CH:58][CH:57]=[CH:56][N:55]=1)#[N:60]

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 8176943-Bromopyridine-2-carbonitrileHCID 21952613HCID 21952613, compoundHCID 67182273(4aS,9bR)-8-amino-6-cyano-3,4,4a,9b-tetrahydro-1H-pyrido[4,3-b]indole-2,5-dicarboxylic acid tert-butyl ester

Product 1

HCID 58700313(4aS,9bR)-8-(2-cyano-pyridin-3-ylamino)-5-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indole-6-carbonitrile

Procedure

The title compound was prepared by following the general method for (5-methyl-6-trifluoromethyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-8-yl)-pyridin-3-yl-amine (Method B) as a yellow solid (35 mg, 35%) from (4aS,9bR)-8-amino-6-cyano-3,4,4a,9b-tetrahydro-1H-pyrido[4,3-b]indole-2,5-dicarboxylic acid tert-butyl ester (Example 162, 100 mg, 0.31 mmol), 3-bromo-pyridine-2-carbonitrile (56 mg, 0.31 mmol) and Cs2CO3 (199 mg, 0.6 mmol). MS (ESI): 331 (base, M+H).

Sources & evidence

ORD record
ord-47e9e23625944c9a9c1d83bf7834acfd
Source dataset
uspto-grants-2006_09
Patent number
US07109339B2

Reaction notes

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