Potassium Phosphate, Tribasic → HCID 178522000, compound

HRID 1748355Notes

Reaction equation

[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21](B5OC(C)(C)C(C)(C)O5)[CH:20]=4)=[O:17])=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[C:43]1[CH:47]=[CH:46][NH:45][N:44]=1>COCCOC.O.C(O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[O:1]=[C:2]1[C:8]2=[CH:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]([NH:18][C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([C:43]5[CH:47]=[CH:46][NH:45][N:44]=5)[CH:20]=4)=[O:17])=[CH:14][C:15]=3[N:7]2[CH2:6][CH2:5][CH2:4][NH:3]1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of 1-oxo-N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxamide in DME:H2O:ethanol (7:3:2 v/v/v, 2.0 mL) is added K3PO4 (34.3 mg, 0.162 mmol) and Pd(dppf)Cl2 CH2Cl2 adduct (11 mg, 0.0135 mmol). The solution is added to a microwave vial containing 3-bromo-1H-pyrazole (29.8 mg, 0.15 mmol). The resulting mixture is heated in a microwave reactor at 150° C. for 30 minutes. The mixture is filtered through Celite (100 mg) washed with ethyl acetate (3×1 mL) and concentrated in vacuo. The residue is purified by mass triggered HPLC to provide the title compound as a (31 mg, 39%).

Workup

additionThe solution is added to a microwave vial
filtrationThe mixture is filtered through Celite (100 mg)
washwashed with ethyl acetate (3×1 mL)
concentrationconcentrated in vacuo
customThe residue is purified by mass

Sources & evidence

ORD record: ord-4493529e2a774900a50071456c2ba1ed
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150577B2

Reaction notes

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