Cesium carbonate → HCID 67258156, compound

HRID 1476631Notes

Reaction equation

HRID 1476631 reaction equation
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[N:7]([CH:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]3)[C:6](=[O:25])[N:5]([CH2:26][C:27]3[O:31][N:30]=[C:29]([CH2:32][CH3:33])[N:28]=3)[C:4]=2[CH:3]=1.[F:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:40]=1[F:41].C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.Cl[Pd]Cl>[F:34][C:35]1[CH:36]=[C:37]([C:2]2[S:10][C:9]3[C:8](=[O:11])[N:7]([CH:12]4[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:16][CH2:17]4)[C:6](=[O:25])[N:5]([CH2:26][C:27]4[O:31][N:30]=[C:29]([CH2:32][CH3:33])[N:28]=4)[C:4]=3[CH:3]=2)[CH:38]=[CH:39][C:40]=1[F:41]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343373,4-Difluorobenzeneboronic acidHCID 67258967Tert-butyl 4-{6-bromo-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate

Product 1

HCID 67258156HCID 67258156, compound

Reagents, catalysts & solvents 2

HCID 11050900Dichlorobis(tricyclohexylphosphine)pallium (II)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Tert-butyl 4-{6-bromo-1-[(3-ethyl-1,2,4-oxadiazol-5-yl)methyl]-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl}piperidine-1-carboxylate (540 mg, compound B99), (3,4-difluorophenyl)boronic acid (158 mg), dichlorobis(tricyclohexylphosphine)palladium (37 mg) and aqueous cesium carbonate solution (489 mg, 2.0 M) in DME (10 ml) are reacted according to the procedure described in example B55 to afford the title compound after purification by flash column chromatography [silica gel, elution gradient: cyclohexane/EtOAc, 70/30 to 50/50 to 30/70 (v/v)] as a solid.

Sources & evidence

ORD record
ord-7943e00a905d42678a9b0d94645438ca
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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