Potassium Phosphate, Tribasic → HCID 71280755, compound

HRID 1497921Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]([NH:13][C:14]3[CH:19]=[C:18]([C:20]4[N:24]=[C:23]([CH:25]5[CH2:28][C:27]([F:30])([F:29])[CH2:26]5)[O:22][N:21]=4)[CH:17]=[CH:16][C:15]=3[CH3:31])=[O:12])=[CH:9][N:10]=2)[CH:7]=1.CC1(C)C(C)(C)OB([C:40]2[CH:41]=[N:42][NH:43][CH:44]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:29][C:27]1([F:30])[CH2:28][CH:25]([C:23]2[O:22][N:21]=[C:20]([C:18]3[CH:17]=[CH:16][C:15]([CH3:31])=[C:14]([NH:13][C:11]([C:8]4[N:6]5[CH:7]=[C:2]([C:40]6[CH:41]=[N:42][NH:43][CH:44]=6)[CH:3]=[CH:4][C:5]5=[N:10][CH:9]=4)=[O:12])[CH:19]=3)[N:24]=2)[CH2:26]1

Participants

Conditions

Temperature: 130 °C

Procedure

6-Bromo-N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (42a) (98.0 mg, 0.2 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (60.0 mg, 0.3 mmol), K3PO4(42.0 mg, 0.2 mmol) and Pd(PPh3)4(46.2 mg, 0.04 mmol) were added to a flask equipped with a stir bar. The flask was evacuated and backfilled with nitrogen several times. 1,4-Dioxane (1 mL) and the reaction was heated at 130° C. for 20 minutes in a microwave reactor. The reaction was filtered and purified by preparative HPLC to afford N-(5-(5-(3,3-difluorocyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)-6-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (F40). MS m/z 476.1 (M+1)+.

Workup

customequipped with a stir bar
customThe flask was evacuated
filtrationThe reaction was filtered
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-d9759897b9fb4a5887eed25416728c2a
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199981B2

Reaction notes

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