Isobutyraldehyde → HCID 22036909, compound

HRID 1294822Notes

Reaction equation

HRID 1294822 reaction equation
[N:1]1([C:6]2[CH:18]=[CH:17][C:9]([O:10][CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)C(C)C.C([Sn](Cl)(Cl)CCCC)CCC.[C:35]1([SiH3])[CH:40]=[CH:39][CH:38]=[CH:37]C=1>C1COCC1>[CH:37]1([N:14]2[CH2:13][CH2:12][CH:11]([O:10][C:9]3[CH:8]=[CH:7][C:6]([N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)=[CH:18][CH:17]=3)[CH2:16][CH2:15]2)[CH2:38][CH2:39][CH2:40][CH2:35]1

Participants

6

Reactant 4

HCID 6561IsobutyraldehydeHCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 220369104-[4-(1H-Imidazol-1-yl)phenoxy]piperidine

Product 1

HCID 22036909HCID 22036909, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 6 (130 mg), isobutyraldehyde (0.06 mL), and dibutyltin dichloride (3 mg) in THF (0.1 mL) was treated with phenylsilane (0.07 mL). After 16 h, the resulting mixture was chromatographed (0–8% 2M methanolic ammonia/DCM), giving the title compound as a waxy solid (57 mg). 1H NMR (400 MHz, CDCl3): 7.75 (t, J=1.2 Hz, 1H), 7.28 (d, J=9.0 Hz, 2H), 7.20 (t, J=1.2 Hz, 1H), 7.17 (t, J=1.2 Hz, 1H), 6.99 (d, J=9.0 Hz, 2H), 4.39–4.29 (m, 1H), 2.87–2.77 (br m, 1H), 2.57–2.48 (m, 1H), 2.40–2.30 (m, 2H), 2.08–1.99 (m, 2H), 1.94–1.82 (m, 5H), 1.75–1.64 (m, 2H), 1.61–1.61 (m, 2H), 1.47–1.37 (m, 2H).

Workup

  1. customthe resulting mixture was chromatographed (0–8% 2M methanolic ammonia/DCM)

Sources & evidence

ORD record
ord-da006e09708a4fdaa616559dee4703de
Source dataset
uspto-grants-2007_07
Patent number
US07241778B2

Reaction notes

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