Cesium carbonate → HCID 73776210, compound

HRID 1052790Notes

Reaction equation

HRID 1052790 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1Br.[OH:29][C:30]1[CH:35]=[CH:34][C:33]([S:36]([NH:39][C:40]2[C:41]([O:55][CH3:56])=[N:42][CH:43]=[C:44](B3OC(C)(C)C(C)(C)O3)[CH:45]=2)(=[O:38])=[O:37])=[CH:32][CH:31]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[NH2:1][C:2]1[C:3]([C:44]2[CH:45]=[C:40]([NH:39][S:36]([C:33]3[CH:32]=[CH:31][C:30]([OH:29])=[CH:35][CH:34]=3)(=[O:38])=[O:37])[C:41]([O:55][CH3:56])=[N:42][CH:43]=2)=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 2733548Bis(pinacolato)diboraneHCID 90103283HCID 90103283, compoundHCID 118433733HCID 118433733, compound

Product 1

HCID 73776210HCID 73776210, compoundYield 52.6%

Procedure

(S)-2-(1-((6-Amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (50 mg, 0.11 mmol) was treated with 4-hydroxy-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide (70 mg, 0.17 mmol) and bis(pinacolato)diboron according to the method described at Preparation 119b), cesium carbonate (2M, 120 μl, 0.24 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (10 mg, 0.01 mmol) according to the method described in Example 3 to give 37 mg (51% yield) of the title compound. Purity 100%.

Sources & evidence

ORD record
ord-ecb19738015e4131b6ef9a036fd28e15
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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