Cesium carbonate → HCID 86726480, compound

HRID 1487647Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]([CH3:12])([OH:11])[CH3:10])[C:6]=1[Cl:7].Cl[C:14]1[N:15]=[C:16]([O:41][CH:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)[C:17]2[C:22]([C:23]3[CH:32]=[CH:31][C:26]4[N:27]=[C:28]([CH3:30])[O:29][C:25]=4[CH:24]=3)=[CH:21][N:20]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:18]=2[N:19]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:7][C:6]1[N:5]([CH2:8][C:9]([CH3:12])([OH:11])[CH3:10])[N:4]=[CH:3][C:2]=1[NH:1][C:14]1[N:15]=[C:16]([O:41][CH:42]2[CH2:43][CH2:44][CH2:45][CH2:46]2)[C:17]2[C:22]([C:23]3[CH:32]=[CH:31][C:26]4[N:27]=[C:28]([CH3:30])[O:29][C:25]=4[CH:24]=3)=[CH:21][N:20]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:18]=2[N:19]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a degassed mixture of 1-(4-amino-5-chloro-1H-pyrazol-1-yl)-2-methylpropan-2-ol (1 equiv), 6-(2-chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1.01 equiv) and 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (0.1 equiv) in 1,4-dioxane (0.08 M) was added palladium acetate (0.1 equiv) and cesium carbonate (3 equiv). The reaction was stirred at 100° C. for 2 h. Upon completion, the reaction mixture was cooled to room temperature and concentrated to give the title compound which was used directly in next step without further purification (97% yield). MS (ESI) m/z 652.2 [M+H]+.

Workup

temperatureUpon completion, the reaction mixture was cooled to room temperature
concentrationconcentrated

Sources & evidence

ORD record: ord-1e0a8ff89e004bfd88bdd49a35dfefeb
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428509B2

Reaction notes

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