Diisobutylaluminum hydride → HCID 66616459, compound

HRID 1917273Notes

Reaction equation

HRID 1917273 reaction equation
C([O:3][C:4]([C:6]1[C:7]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)=[N:8][C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:10][CH:11]=1)=O)C.CC(C[AlH]CC(C)C)C>C1COCC1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:9]2[N:8]=[C:7]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=3)[C:6]([CH2:4][OH:3])=[CH:11][N:10]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 66616382HCID 66616382, compound

Product 1

HCID 66616459HCID 66616459, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 9855836Potassium sodium tartarateSolvent

Procedure

To a 0° C. solution of the product from Step A (0.606 g, 1.73 mmol) in THF (8 mL) was added DIBAL-H (1.5 M in toluene; 2.5 mL, 3.8 mmol). The mixture was allowed to warm to rt, and was stirred for 18 h. The mixture was diluted with 20% aq. sodium potassium tartrate and extracted with EtOAc (2×). The combined organic layers were dried and concentrated. The resulting residue was purified via SiO2 chromatography (40-60% EtOAc/hexanes) to give 0.330 g (62%) of the title compound. MS (ESI): exact mass calcd. for C19H17FN2O, 308.13; m/z found, 309.4 [M+H]+. 1H NMR (CDCl3): 8.77 (s, 1H), 7.58 (d, J=8.0, 2H), 7.38-7.35 (m, 2H), 7.29 (d, J=7.9, 2H), 6.99-6.96 (m, 2H), 4.70 (s, 2H), 4.29 (s, 2H), 2.42 (s, 3H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. customThe resulting residue was purified via SiO2 chromatography (40-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-beaab773802148d0a7f94eedee005507
Source dataset
uspto-grants-2013_12
Patent number
US08618288B2

Reaction notes

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