Potassium Sodium Tartrate → HCID 68771531, compound

HRID 1947493Notes

Reaction equation

HRID 1947493 reaction equation
COC([C:5]1[O:6][C:7]2[CH:13]=[C:12]([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:11]=[CH:10][C:8]=2[CH:9]=1)=O.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)[C:35]([O-])=[O:36].[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:12]1[CH:11]=[CH:10][C:8]2[C:9]([CH2:35][OH:36])=[CH:5][O:6][C:7]=2[CH:13]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 68772924HCID 68772924, compound

Product 1

HCID 68771531HCID 68771531, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-2-carboxylic acid methyl ester (6.0 g, 18.3 mmol) in DCM (183 mL) was added DIBALH (1 M in THF, 54.8 mL, 54.8 g, 54.8 mmol) and the reaction mixture was stirred (0° C., 1 h). The reaction mixture was treated with saturated aqueous Rochelle's salt (100 mL) and partitioned with DCM (50 mL). The organic layer was separated and the aqueous layer was extracted with DCM (2×100 mL). The organic layer was dried, filtered and concentrated in vacuo to provide the title compound as yellow solid (4.9 g, 90%). MS (ESI): mass calcd. for C16H10N2O3S, 298.04; m/z found, 299.0 [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), 8.00 (s, 1H), 7.86 (d, J=2.1, 1H), 7.84 (s, 1H), 7.45-7.37 (m, 1H), 7.38-7.31 (m, 1H), 5.25 (t, J=5.5, 1H), 4.67 (dd, J=5.5, 0.8, 2H).

Workup

  1. custompartitioned with DCM (50 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with DCM (2×100 mL)
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a271585cb77246abbd5f781e38779c03
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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