Diisobutylaluminumhydride → HCID 11648654, compound

HRID 2353826Notes

Reaction equation

HRID 2353826 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]2[C:12]3[C:17]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=5)=[C:21]([Cl:34])[CH:20]=4)=[N:16][CH:15]=[N:14][C:13]=3[S:35][C:8]=2[CH:7]=1)C.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[Cl:34][C:21]1[CH:20]=[C:19]([NH:18][C:17]2[C:12]3[C:9]4[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][OH:3])=[CH:7][C:8]=4[S:35][C:13]=3[N:14]=[CH:15][N:16]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 59380413HCID 59380413, compound

Product 1

HCID 11648654HCID 11648654, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)[1]benzothieno[2,3-d]pyrimidin-7-yl]acetate (858 mg, 1.64 mmol, 1 equiv) in THF (10 mL) was added 1M solution of diisobutylaluminum hydride in hexanes (6.6 mL, 6.57 mmol, 4 equiv) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 1 h. The reaction mixture was quenched with Rochelle's salt followed by extraction with EtOAc (3×50 mL). The combined organic layers were washed with brine (100 mL) and water (100 mL), dried over sodium sulfate and concentrated in vacuo. The crude material was purified by flash chromatography (40% EtOAc/hexane then 100% EtOAc) to yield a light yellow (845 mg, 48%). 1H-NMR (CD3OD) δ 8.35 (s, 1H), 8.18 (d, J=8.6 Hz, 1H), 7.76 (s, 1H), 7.71 (d, J=2.0 Hz, 1H), 7.43-7.34 (m, 3H), 7.27-7.20 (m, 2H), 7.03 (m, 2H), 5.12 (s, 2H), 3.83 (t, 2H), 2.95 (t, 2H); LCMS RT=3.56 min, [M+H]+=480

Workup

  1. customThe reaction mixture was quenched with Rochelle's salt
  2. extractionfollowed by extraction with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with brine (100 mL) and water (100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (40% EtOAc/hexane
  7. custom100% EtOAc) to yield a light yellow (845 mg, 48%)

Sources & evidence

ORD record
ord-8036858761824a51afe326f68fef000a
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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