Potassium Sodium Tartrate → [6-(Thiazolo[4,5-b]pyridin-2-yloxy)-benzo[b]thiophen-2-yl]-methanol

HRID 1947488Notes

Reaction equation

C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[C:11]([O:14][C:15]3[S:16][C:17]4[C:18]([N:23]=3)=[N:19][CH:20]=[CH:21][CH:22]=4)[CH:12]=[CH:13][C:7]=2[CH:6]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[S:16]1[C:17]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[N:23]=[C:15]1[O:14][C:11]1[CH:12]=[CH:13][C:7]2[CH:6]=[C:5]([CH2:3][OH:2])[S:9][C:8]=2[CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of 6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzo[b]thiophene-2-carboxylic acid methyl ester (0.18 g, 0.5 mmol) in DCM (5 mL) was added LAH (2 M in THF, 0.3 mL, 0.3 g, 0.5 mmol) and the reaction mixture was stirred (0° C., 1 h). The reaction mixture was treated with saturated aqueous Rochelle's salt (2 mL) and partitioned with EtOAc (15 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×15 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as an orange solid (0.13 mg, 82%). MS (ESI): mass calcd. for C15H10O2S2, 314.0; m/z found, 315.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (dd, J=4.8, 1.7, 1H), 8.02 (dd, J=7.9, 1.6, 1H), 7.95 (d, J=2.2, 1H), 7.76 (d, J=8.7, 1H), 7.38 (dd, J=8.6, 2.3, 1H), 7.21 (dd, J=7.9, 4.9, 2H), 4.94 (s, 2H), 2.14 (s, 1H).

Workup

custompartitioned with EtOAc (15 mL)
customThe organic layer was separated
extractionthe aqueous layer was extracted with EtOAc (2×15 mL)
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-dfa114c401574ec688607e40bccb9145
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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