Potassium Carbonate → HCID 178487938, compound

HRID 449057Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:22]3[CH:23]=[CH:24][N:25]=[C:26]([NH2:27])[C:21]3=[C:20](I)[N:19]=2)[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][O:31][C:32]1[CH:33]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:35]=[CH:36][C:37]=1[O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O>[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH2:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([C:18]2[N:22]3[CH:23]=[CH:24][N:25]=[C:26]([NH2:27])[C:21]3=[C:20]([C:34]3[CH:35]=[CH:36][C:37]([O:38][C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)=[C:32]([O:31][CH3:30])[CH:33]=3)[N:19]=2)[CH2:14][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of trans-[4-(8-amino-1-iodo-imidazo[1,5-a]pyrazin-3-yl)-cyclohexylmethyl]-carbamic acid benzyl ester (80.0 mg, 0.0002 mol), 2-(3-methoxy-4-phenoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (67.0 mg, 0.0002 mol), potassium carbonate (0.076 g, 0.00055 mol) in DME (3.00 mL) and H2O (0.50 mL) was added 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride DCM (9.0 mg, 0.00001 mol). The resulting mixture was stirred at 100° C. for 2 h under nitrogen atmosphere. Solvent was removed under reduced pressure and the product was purified by flash chromatography (2% MeOH in DCM). MS (ES+): m/z: 577.95 [MH+]. HPLC: tR=2.72 min (OpenLynx: polar—5 min).

Workup

customSolvent was removed under reduced pressure
customthe product was purified by flash chromatography (2% MeOH in DCM)
customHPLC: tR=2.72 min (OpenLynx: polar—5 min)

Sources & evidence

ORD record: ord-efa4d25ad3924a12b7e488b8a164cb33
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481733B2

Reaction notes

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