Potassium Phosphate, Tribasic → HCID 178516433, compound

HRID 1784812Notes

Reaction equation

C(OC1N=CC([NH:15][C:16]2[CH:21]=[C:20]([C:22]3[CH:30]=[CH:29][CH:28]=[C:27]4[C:23]=3[CH:24]=[CH:25][N:26]4[Si](C(C)C)(C(C)C)C(C)C)C=C(OCC3C=CC(OC)=CC=3)[CH:17]=2)=CC=1)C1C=CC=CC=1.C([O:58][C:59]1[N:64]=[CH:63][C:62](NC2C=C(OCC3C=CC(OC)=CC=3)C=C(Br)C=2)=[CH:61][CH:60]=1)C1C=CC=CC=1.[CH3:83][C:84]1(C)C(C)(C)OB(C2C=CC=C3C=2C=CN3[Si](C(C)C)(C(C)C)C(C)C)[O:85]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.Cl[Pd-](P(C1CC2CC1CC2)C1CC2CC1CC2)C1C=CC=CC=1C1C=CC=CC=1N(C)C>[OH:85][C:84]1[CH:17]=[C:16]([NH:15][C:60]2[C:59]([OH:58])=[N:64][CH:63]=[CH:62][CH:61]=2)[CH:21]=[C:20]([C:22]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:23]=2[CH:24]=[CH:25][NH:26]3)[CH:83]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(6-benzyloxy-pyridin-3-yl)-[3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-amine. To a tube purged with nitrogen containing (6-benzyloxy-pyridin-3-yl)-[3-bromo-5-(4-methoxy-benzyloxy)-phenyl]-amine (78 mg, 0.158 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (63 mg, 0.158 mmol) and chloro(di-2-norbornylphosphino)(2′dimethylamino-1,1′-biphenyl-2-yl)palladium (II) (9.0 mg, 0.0158 mmol) in dioxane (2 mL) was added 2M aqueous K3PO4 (0.16 mL, 0.32 mmol). The tube was sealed and heated in a microwave reactor at 120° C. for an hour. The crude mixture was loaded directly to Celite®, and purified by chromatography to afford the -[3-hydroxy-5-(1H-indol-4-yl)-phenylamino]-pyridin-2-ol as a white solid (62 mg, 57.1%).

Workup

customTo a tube purged with nitrogen
customThe tube was sealed
custompurified by chromatography

Sources & evidence

ORD record: ord-0d8a05038e0b418682bb41b4051f3946
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504401B2

Reaction notes

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