Dimethylformamide → 5,6-Dihydro-6-hydroxy-5,5-dimethyl-7-(4-trifluoromethylbenzamido)-7H-thieno[3,2-b]pyran

HRID 1086646Notes

Reaction equation

Br[CH:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][S:12][C:4]=2[CH:3]1O.[F:14][C:15]([F:26])([F:25])[C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH2:22])=[O:21])=[CH:18][CH:17]=1.[K+].[Br-].CN(C)C=[O:32]>>[OH:32][CH:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][S:12][C:4]=2[CH:3]1[NH:22][C:20](=[O:21])[C:19]1[CH:23]=[CH:24][C:16]([C:15]([F:25])([F:26])[F:14])=[CH:17][CH:18]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 746844-(Trifluoromethyl)benzamide

HCID 253877Potassium Bromide

HCID 149864866-bromo-5,6-dihydro-7-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran

Product 1

HCID 149865085,6-Dihydro-6-hydroxy-5,5-dimethyl-7-(4-trifluoromethylbenzamido)-7H-thieno[3,2-b]pyran

Procedure

The title compound was prepared as described in Example 3 starting with 6-bromo-7-hydroxy-5,6-dihydro-5,5-dimethyl-7H-thieno[3,2-b]pyran (4.5 g, 17.1 mmol) and 4-trifluoromethylbenzamide (7.43 g, 39.3 mmol) in N,N-dimethylformamide (75 mL) to give the product, 1.96 g (31%), as a colorless solid: mp 162°-163° C.; IR (KBr): 3396, 1664, 1534 and 1507 cm-1 ; MS: m/z 372 (MH+); 1H NMR (DMSO-d6): δ1.21(s, 3H), 1.40(s, 3H), 3.80(m, 1H, simplifies to d, J=8.7 Hz, with D2O), 5.01(m, 1H, simplifies to d, J=8.7 Hz, with D2O), 5.68(d, J=6.0 Hz, 1H, exchanges with D2O), 6.59(d, J 5.7 Hz, 1H), 7.31(d, J=5.7 Hz, 1H), 7.88(d, J=8.3 Hz, 2H), 8.11(d, J=8.3 Hz, 2H) and 9.05(d, J=8.4 Hz, 1H exchanges with D2O).

Workup

customto give the product, 1.96 g (31%)

Sources & evidence

ORD record: ord-f267e6037543412f8020e6a9a228c15a
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05030736

Reaction notes

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