Acetone → HCID 18383075, compound

HRID 2297832Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[CH:20]=[C:21]([C:23]3[S:24][CH:25]=[CH:26][N:27]=3)[S:22][C:15]=12.[CH3:28][C:29]([CH3:31])=[O:30]>O1CCCC1.O>[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[CH:20]=[C:21]([C:23]3[S:24][C:25]([C:29]([OH:30])([CH3:31])[CH3:28])=[CH:26][N:27]=3)[S:22][C:15]=12

Participants

Conditions

Temperature: 0 °C

Procedure

In a 25 mL round-bottomed flask 2 mL of tetrahydrofuran and diisopropyl amine (0.14 mL, 1.0 mmol) were cooled to −78° C. and n-butyllithium (0.38 mL, 0.95 mmol) was added. The solution was warmed to 0° C. for 10 minutes then recooled to −78° C. A solution of 7-chloro-2-thiazol-2-yl-thieno[3,2-b]pyridine (200 mg, 0.79 mmol) in 2 mL of tetrahydrofuran was added dropwise and the resulting solution was stirred 30 minutes. Acetone (0.88 mL, 1.19 mmol) was added to the anion and the reaction mixture was allowed to warm to room temperature overnight. The mixture was diluted with water and extracted with chloroform (3×50 mL). The combined extracts were dried over NaSO4, filtered, and concentrated. Chromatography on 50 g of silica gel with 30% ethyl acetate:methylene chloride afforded 129 mg (52%) 2-[2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-thiazol-5-yl]-propan-2-ol. 1H NMR (400 MHz, CD3OD) δ8.56 (d, 1H), 7.95 (s, 1H), 7.71 (s, 1H), 7.50 (d, 1H), 1.66 (s, 6H). LC-MS: 308.1, 311 (MH+); HPLC RT: 5.32 min.

Workup

customthen recooled to −78° C
temperatureto warm to room temperature overnight
extractionextracted with chloroform (3×50 mL)
dry with materialThe combined extracts were dried over NaSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-01bca5a1fe4847929520ef6d96ae4828
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492383B1

Reaction notes

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