Potassium Phosphate, Tribasic → (6-Cyclopropyl-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester

HRID 908232Notes

Reaction equation

[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[C:13](Br)=[CH:12][N:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:17]=[C:10]2[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:25]1(B(O)O)[CH2:27][CH2:26]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[C:13]([CH:25]2[CH2:27][CH2:26]2)=[CH:12][N:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:17]=[C:10]2[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester (Example 67, Step 1-3, 600 mg, 1.54 mmol), cyclopropylboronic acid (265 mg, 3.12 mmol), potassium phosphate (1.64 g), tricyclohexylphosphine (95 mg), and palladium(II) acetate (38 mg) were placed in a round-bottom flask, and the flask was filled with an atmosphere of Argon. Toluene (15 ml) and water (1 ml) were added and the mixture was heated to 100° C. overnight. Upon cooling, the reaction mixture was taken up in ethyl acetate and washed. The organic layers were dried (Na2SO4) and evaporated. The title compound (470 mg, 87%) was isolated from the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40). MS (m/e)=350.4 [M+H+].

Workup

additionthe flask was filled with an atmosphere of Argon
temperatureUpon cooling
washwashed
dry with materialThe organic layers were dried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-878e1ccd447f48349adeb0716652d676
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017604B2

Reaction notes

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