Hydrochloric Acid → HCID 67314715, compound

HRID 1254082Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH3:11][C:12]1[N:17]=[C:16]2[CH2:18][O:19][C:20](=O)[C:15]2=[CH:14][CH:13]=1.Cl>C1COCC1>[CH3:11][C:12]1[N:17]=[C:16]2[CH2:18][O:19][C:20](=[C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][C:2]3=[O:10])[C:15]2=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 1,3-dihydro-indol-2-one (200 mg, 1.5 mmol.) in THF (2 mL) is placed under an argon atmosphere and cooled in an ice bath. A solution of Li bis(trimethylsilyl)amide (4.0 mL of a 1M solution in THF, 4.0 mmol) is added slowly at 0° C. and the resulting solution is stirred for 10 min. The ice-bath is then removed and a solution of 2-methyl-7H-furo[3,4-b]pyridin-5-one (150 mg, 1.00 mmol) in THF (6 mL) is added dropwise to the reaction mixture. The resulting solution is stirred for 4 h and then poured into 10% aqueous HCl solution (50 mL). After 10 min at room temperature, the reaction is heated to ˜90° C. for 45 min followed by stirring at room temperature for 36 h. The solid which precipitated from solution is collected by filtration and washed sequentially with small volumes of MeOH, EtOAc, Et2O and dried under vacuum to give the title compound as a yellow solid (78 mg, 30%).

Workup

temperaturecooled in an ice bath
customThe ice-bath is then removed
stirringThe resulting solution is stirred for 4 h
waitAfter 10 min at room temperature
stirringby stirring at room temperature for 36 h
customThe solid which precipitated from solution
filtrationis collected by filtration
washwashed sequentially with small volumes of MeOH, EtOAc, Et2O
customdried under vacuum

Sources & evidence

ORD record: ord-8a171349c069405a98fa40c7393118cf
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455535B2

Reaction notes

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