Diisobutylaluminum hydride → [6-(Thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-yl]-methanol

HRID 1947473Notes

Reaction equation

HRID 1947473 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([O:15][C:16]3[S:17][C:18]4[C:19]([N:24]=3)=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:12]=[CH:11][C:9]=2[CH:10]=1)=O)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[S:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][CH:23]=2)[N:24]=[C:16]1[O:15][C:13]1[CH:12]=[CH:11][C:9]2[CH:10]=[C:6]([CH2:4][OH:3])[O:7][C:8]=2[CH:14]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 687707006-(Thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 59577541[6-(Thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-yl]-methanolYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution 6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-carboxylic acid ethyl ester (300 mg, 0.8 mmol) in DCM (8 mL) was added DIBALH (1 M in THF, 3 mL, 3 mmol) and the reaction mixture was warmed (rt, 48 h). The reaction mixture was quenched with saturated aqueous Rochelle's Salt (2 mL) and partitioned with DCM. The organic layer was separated and the aqueous layer was extracted with DCM (2×15 mL). The organic layers were combined, dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using MeOH:DCM (0-10%) to provide the title compound as a yellow solid (197 mg, 82%). MS (ESI): mass calcd. for C16H10N2O3S, 298.1; m/z found, 299.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 8.53 (dd, J=4.8, 1.7, 1H), 8.40 (dd, J=8.0, 1.7, 1H), 7.84 (d, J=1.7, 1H), 7.74 (d, J=8.4, 1H), 7.44-7.26 (m, 2H), 6.86 (s, 1H), 5.54 (t, J=5.9, 1H), 4.60 (d, J=5.9, 2H).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous Rochelle's Salt (2 mL)
  2. custompartitioned with DCM
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with DCM (2×15 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-c924b8157adf4b2e83e4c5a0141c4db1
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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