Sodium triacetoxyborohydride → HCID 67271631, compound

HRID 1592691Notes

Reaction equation

HRID 1592691 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH2:11][NH:12][CH:13]1[C:22]2[N:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:16][CH2:15][CH2:14]1)[C:6]#[N:7].[C:23]1([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([CH:35]=O)[CH:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[CH2:11][N:12]([CH2:35][C:31]1[CH:30]=[C:29]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:34]=[CH:33][N:32]=1)[CH:13]1[C:22]2[N:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:16][CH2:15][CH2:14]1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 122176544-Phenylpyridine-2-carboxaldehydeHCID 67271659HCID 67271659, compound

Product 1

HCID 67271631HCID 67271631, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using General Procedure B: Reaction of 3-hydroxymethyl-4-[(5,6,7,8-tetrahydro-quinolin-8-ylamino)-methyl]-benzonitrile in CH2Cl2 with 4-phenyl-pyridine-2-carbaldehyde and NaBH(OAc)3 gave 3-hydroxymethyl-4-{[(4-phenyl-pyridin-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzonitrile as a colorless oil. 1H NMR (CDCl3) δ 1.63 (m, 1H), 2.08 (m, 2H), 2.29 (m, 1H), 2.72 (m, 1H), 2.81 (m, 1H), 3.61 (d, 1H, J=12.0 Hz), 3.73 (d, 1H, J=12.0 Hz), 3.85 (m, 3H), 4.08-4.23 (m, 3H), 4.43 (d, 1H, J=9.0 Hz), 7.06 (dd, 1H, J=7.5, 3.0 Hz), 7.36-7.64 (m, 8H), 7.86 (d, 2H, J=9.0 Hz), 8.00 (s, 1H), 8.51 (dd, 2H, J=12.0, 4.5 Hz).

Sources & evidence

ORD record
ord-62b357f3a0db4eb1b672d3fce8df5393
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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