Cesium carbonate → HCID 178429110, compound

HRID 2173911Notes

Reaction equation

[NH2:1][C:2]([C:15]1[C:23]([O:24][CH:25]([F:27])[F:26])=[CH:22][C:21]([CH3:28])=[C:20]2[C:16]=1[CH:17]=[CH:18][N:19]2C(OC(C)(C)C)=O)([C:4]1[NH:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]#[N:14])=[CH:12][C:6]=2[N:5]=1)[CH3:3].C([O-])([O-])=O.[Cs+].[Cs+]>CO>[NH2:1][C:2]([C:4]1[NH:8][C:7]2[CH:9]=[CH:10][C:11]([C:13]#[N:14])=[CH:12][C:6]=2[N:5]=1)([C:15]1[C:23]([O:24][CH:25]([F:26])[F:27])=[CH:22][C:21]([CH3:28])=[C:20]2[C:16]=1[CH:17]=[CH:18][NH:19]2)[CH3:3]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of tert-butyl 4-(1-amino-1-(5-cyano-1H-benzo[d]imidazol-2-yl)ethyl)-5-(difluoromethoxy)-7-methyl-1H-indole-1-carboxylate (77 mg, 0.160 mmol) in MeOH (1.6 mL) at room temperature, Cs2CO3 (261 mg, 0.8 mmol) was added and the reaction was stirred at 60° C. After 1 hour the reaction mixture was loaded directly onto a silica gel column and purified by flash chromatography (0-100% EtOAc in heptanes) to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.19 (br. s., 1H) 7.96 (br. s., 1H) 7.58 (br. s., 1H) 7.50 (dd, J=8.21, 1.39 Hz, 1H) 7.28 (t, J=2.91 Hz, 1H) 6.70 (s, 1H) 6.66 (t, J=75.3 Hz, 1H) 6.45 (br. s., 1H) 2.45 (d, J=0.76 Hz, 3H) 2.00 (s, 3H). HRMS calcd. for C20H17F2N5O (M+H)+ 382.1474. found 382.1486.

Workup

custompurified by flash chromatography (0-100% EtOAc in heptanes)

Sources & evidence

ORD record: ord-4fe7396a0ad446819be687cbb8cbf97c
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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