Diisobutylaluminum hydride → HCID 71657341, compound

HRID 591349Notes

Reaction equation

HRID 591349 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][C:22]([C:25](OC)=[O:26])=[CH:23][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][C:22]([CH2:25][OH:26])=[CH:23][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 89612782HCID 89612782, compound

Product 1

HCID 71657341HCID 71657341, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of methyl 2-(4-(6-fluoroindolin-1-yl)piperidine-1-carboxamido)thiazole-5-carboxylate (80.8 mg, 0.2 mmol, 1 equiv) in dried CH2Cl2 (5 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 90-100% EtOAc/hexane as the eluent to yield 4-(6-fluoroindolin-1-yl)-N-(5-(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-d2739a6ef3af4463a4cab1344c13e7e4
Source dataset
uspto-grants-2016_01
Patent number
US09238658B2

Reaction notes

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