Diisobutylaluminum hydride → 3-Methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

HRID 1177458Notes

Reaction equation

HRID 1177458 reaction equation
CC(C[AlH]CC(C)C)C.[CH3:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[C:19]1[S:20][C:21]2[C:26]([N:27]=1)=[CH:25][CH:24]=[C:23]([C:28]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:30][CH2:29]1)[N:22]=2)[C:14]#N.C(C(C(C([O-])=O)O)O)([O-])=[O:38]>C(Cl)Cl>[CH3:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[C:19]1[S:20][C:21]2[C:26]([N:27]=1)=[CH:25][CH:24]=[C:23]([C:28]1([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:30][CH2:29]1)[N:22]=2)[CH:14]=[O:38]

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydride2×HCID 38061142,3-DihydroxybutanedioateHCID 671116823-Methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzonitrile

Product 1

HCID 866387133-Methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

DIBAL-H (11.0M in hexanes; 315 μl, 315 μmol) was added to a solution of 3-methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzonitrile (105.2 mg, 286 μmol) in CH2Cl2 (4.5 mL) at 25° C., and the resulting solution was stirred at 25° C. for 45 min. Additional DIBAL-H (1.0M in hexanes; 86 μL, 86 μmol) was then added, and the resulting solution was stirred at 25° C. for 30 min. Saturated aqueous Na/K tartrate solution (4.0 mL) was added, and the resulting mixture was vigorously stirred for 15 min, then partitioned between CH2Cl2 (40 mL) and saturated. Aqueous Na/K tartrate solution (10 mL). The organic layer was separated, and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-40% EtOAc/hexanes) provided 3-methyl-4-(5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine-2-yl)-benzaldehyde as a light-yellow foam. MS (ESI) m/z: Calculated: 370.1; Observed: 371.1 (M++1).

Workup

  1. stirringthe resulting solution was stirred at 25° C. for 30 min
  2. stirringthe resulting mixture was vigorously stirred for 15 min
  3. custompartitioned between CH2Cl2 (40 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with CH2Cl2
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customChromatographic purification of the residue (silica gel, 0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-1c3e8f064fc94d0eac49fb4b9f2329a8
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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