Ethyl Acetate → HCID 10300103, compound

HRID 1278827Notes

Reaction equation

[Br:1][C:2]1[C:11]2[S:12][C:13]([CH3:16])=[C:14]([CH3:15])[C:10]=2[C:9]([C:17]2[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[C:19]([Br:26])[C:18]=2OC)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[CH:7]2.[Sn](Cl)Cl.[C:32](OCC)(=[O:34])C>>[Br:26][C:19]1[C:20]([O:34][CH3:32])=[C:21]([NH2:23])[CH:22]=[C:17]([C:9]2[C:10]3[C:14]([CH3:15])=[C:13]([CH3:16])[S:12][C:11]=3[C:2]([Br:1])=[C:3]3[C:8]=2[CH:7]=[CH:6][CH:5]=[CH:4]3)[CH:18]=1

Participants

Reactant 3

HCID 8857Ethyl Acetate2×

HCID 24479Stannous Chloride

HCID 69872574HCID 69872574, compound

Product 1

HCID 10300103HCID 10300103, compoundYield 92%

Conditions

Temperature: 70 °C

Procedure

A stirred suspension of 9-bromo-4-(3-bromo-methoxy-5-nitro-phenyl)-2,3-dimethyl-naphtho[2,3-b]thiophene (0.372, 0.714 mmol), tin (II) dichloride (805 mg, 3.57 mmol) and ethyl acetate (4 mL)was heated to 70° C. where disolution occured. After 30 min, the reaction mixture was cooled to room temperature, diluted with ethyl acetate and silica gel was added. The ethyl acetate was removed and the adsorbate was flash chromatographed (4:1 pet. ether:ethyl acetate) to provide the title compound as a white solid (0.324 g, 92%): mp 198-200° C.: NMR (DMSO-d6); 8.18 (d, J=8 Hz, 1H), 7.64 (ddd, J=8, 6, 1 Hz, 1H), 7.58 (d, J=8 Hz, 1H), 7.50 (ddd, J=8, 6, 1 Hz, 1H), 6.70 (d, J=2 Hz, 1H), 6.64 (d, J=2 Hz, 1H), 5.46 (s, 1H), 3.80 (s, 3H), 2.44 (d, J=1 Hz, 3H), 1.73 (d, J=1 Hz, 3H); MS (EI): 2 bromine isotope pattern 489 (50%, M+), 491 (100%, M+), 493 (60%, M+); Anal. Calc. for C21H17Br2NOS: C, 51.34, H, 3.49, N, 2.85. Found: C, 51.00, H, 3.43, N, 2.71.

Workup

temperaturethe reaction mixture was cooled to room temperature
additionwas added
customThe ethyl acetate was removed
customchromatographed (4:1 pet. ether:ethyl acetate)

Sources & evidence

ORD record: ord-726bb83d7341410ebe0de4a21cca98f1
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06444670B2

Reaction notes

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