4-Fluorobenzoyl chloride → HCID 89690731, compound

HRID 710254Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]3[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]3)=[CH:8][CH:9]=2)[NH:4][N:3]=1.[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>N1C=CC=CC=1>[F:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH:1][C:2]2[C:10]3[C:5](=[CH:6][C:7]([CH:11]4[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12]4)=[CH:8][CH:9]=3)[NH:4][N:3]=2)=[O:30])=[CH:27][CH:26]=1

Participants

Conditions

Temperature: -5 °C

Procedure

Tert-butyl 2-(3-amino-1H-indazol-6-yl)morpholine-4-carboxylate (43 mg, 0.135 mmol) was dissolved in pyridine (0.2 ml) and the solution was cooled to −5° C. 4-fluorobenzoyl chloride (21.4 mg, 0.135 mmo) was slowly added. After 5 min, the cooling bath was removed and stirring was continuing overnight. The reaction mixture was diluted with ethylacetate (2 ml) and washed with 1M citric acid solution (2 ml). The organic layer was dried over MgSO4 and concentrated in vacuo to give a brown oil which was further purified by flash column chromatography (silica gel, 50% to 100% ethyl acetate in heptane). The product was isolated as a yellow solid (40 mg, 67%), MS (ISP): 441.3 (100%, ([M-tBu+H]+), 385.2 (38%, [M+H]+).

Workup

customthe cooling bath was removed
waitwas continuing overnight
additionThe reaction mixture was diluted with ethylacetate (2 ml)
washwashed with 1M citric acid solution (2 ml)
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
customto give a brown oil which
customwas further purified by flash column chromatography (silica gel, 50% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-8f0cb09a32944b7aa7787d88b1dedb8d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181230B2

Reaction notes

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