Diisobutylaluminum hydride → HCID 71657340, compound

HRID 591348Notes

Reaction equation

HRID 591348 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]3[S:21][CH:22]=[C:23]([C:25](OCC)=[O:26])[N:24]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.C(O)(=O)C(C(C(O)=O)O)O.[Na]>C(Cl)Cl>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][N:8]2[CH:11]2[CH2:16][CH2:15][N:14]([C:17]([NH:19][C:20]3[S:21][CH:22]=[C:23]([CH2:25][OH:26])[N:24]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 45051801HCID 45051801, compoundHCID 89612672HCID 89612672, compound

Product 1

HCID 71657340HCID 71657340, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of ethyl 2-(4-(6-fluoroindolin-1-yl)piperidine-1-carboxamido)thiazole-4-carboxylate (83.6 mg, 0.2 mmol, 1 equiv) in dried CH2Cl2 (3 mL) under N2 at room temperature was then slowly added DIBAL-H (1M in CH2Cl2, 1 mL, 1 mmol, 5 equiv). The resulting mixture became a clear solution and was stirred at room temperature for 1 h. The resulting mixture was slowly poured into a vigorously stirred mixture of CH2Cl2/10 wt % sodium tartaric acid (aq.) (10 mL/10 mL). The resulting mixture was stirred for 1 h and the layers were separated. The aqueous layer was extracted with CH2Cl2 (30 mL). The combined organic layer was dried (Na2SO4) and filtered. The solvent was removed by roto-evaporator and the resulting residue purified by column using 80-90% EtOAc/hexane as the eluent to yield 4-(6-fluoroindolin-1-yl)-N-(4-(hydroxymethyl)thiazol-2-yl)piperidine-1-carboxamide.

Workup

  1. stirringThe resulting mixture was stirred for 1 h
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 (30 mL)
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customThe solvent was removed by roto-evaporator
  7. customthe resulting residue purified by column

Sources & evidence

ORD record
ord-5de3c7fc9cac4c53b7e44b6b61db1cb6
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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