Benzyl Bromide → 7-Benzyl-2-cyclopropyl-5,6,7,8-tetrahydro-1,7-naphthyridine

HRID 2284446Notes

Reaction equation

Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][N:6]=[CH:7][CH:8]=2)[N:3]=1.[CH:12]1(B(O)O)[CH2:14][CH2:13]1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+]>>[CH2:18]([N:6]1[CH2:5][C:4]2[N:3]=[C:2]([CH:12]3[CH2:14][CH2:13]3)[CH:11]=[CH:10][C:9]=2[CH2:8][CH2:7]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Reactant 4

HCID 7498Benzyl Bromide

HCID 2760897Cyclopropylboronic acid

HCID 4311764Sodium borohydride

HCID 206966252-Chloro-1,7-naphthyridine

Product 1

HCID 1176782537-Benzyl-2-cyclopropyl-5,6,7,8-tetrahydro-1,7-naphthyridine

Procedure

2-Chloro-1,7-naphthyridine was subjected to a Suzuki reaction with cyclopropylboronic acid; the product was reacted with benzyl bromide, and then reduced with sodium borohydride to afford 7-benzyl-2-cyclopropyl-5,6,7,8-tetrahydro-1,7-naphthyridine. Protecting group removal with 1-chloroethyl carbonochloridate provided 2-cyclopropyl-5,6,7,8-tetrahydro-1,7-naphthyridine.

Sources & evidence

ORD record: ord-91741be09bab4ab3b6d38351e138ca54
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145427B2

Reaction notes

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