Cesium carbonate → HCID 59326885, compound

HRID 1880094Notes

Reaction equation

HRID 1880094 reaction equation
[F:1][CH:2]([F:16])[C:3]1([C:9]2[C:10](F)=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[C:32]([C:34]1[CH:39]=[CH:38][C:37]([OH:40])=[CH:36][CH:35]=1)=[O:33]>CN1C(=O)CCC1>[NH:23]1[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[N:25]=[C:24]1[C:32]([C:34]1[CH:39]=[CH:38][C:37]([O:40][C:10]2[C:9]([C:3]3([CH:2]([F:16])[F:1])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]3)=[CH:14][CH:13]=[CH:12][N:11]=2)=[CH:36][CH:35]=1)=[O:33]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 59326778HCID 59326778, compoundHCID 59326874(1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone

Product 1

HCID 59326885HCID 59326885, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
175 °C

Procedure

To a solution of 3-(4-(difluoromethyl)tetrahydro-2H-pyran-4-yl)-2-fluoropyridine (0.1 g, 0.432 mmol) in NMP was added cesium carbonate (0.282 g, 0.865 mmol) and (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (0.155 g, 0.649 mmol). The resulting mixture was heated to 175° C. overnight. Purification by prep-plate TLC (5% MeOH/DCM & 75% EtOAc/hexane) produced product. MS (ESI, pos. ion) m/z: 450 (M+1). IC50 (uM) +++++.

Workup

  1. customPurification by prep-plate TLC (5% MeOH/DCM & 75% EtOAc/hexane)
  2. customproduced product

Sources & evidence

ORD record
ord-d2665ff2f0ab4d7d82d83065951707d8
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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