2-(2,5-Dihydrofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → (Racemic) 7-(dimethoxymethyl)-6-(tetrahydrofuran-3-yl)-1,2,3,4-tetrahydro-1,8-naphthyridine

HRID 1778066Notes

Reaction equation

HRID 1778066 reaction equation
[CH3:1][O:2][CH:3]([O:20][CH3:21])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][C:5]=1[CH:14]1[CH2:19][CH2:18][O:17][CH2:16]C1.O1CC=C(B2OC(C)(C)C(C)(C)O2)C1>>[CH3:21][O:20][CH:3]([O:2][CH3:1])[C:4]1[N:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][C:5]=1[CH:14]1[CH2:19][CH2:18][O:17][CH2:16]1

Participants

3

Reactant 2

HCID 108672332-(2,5-Dihydrofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 1180366867-(Dimethoxymethyl)-1,2,3,4-tetrahydro-6-(tetrahydro-2H-pyran-4-yl)-1,8-naphthyridine

Product 1

HCID 118036983(Racemic) 7-(dimethoxymethyl)-6-(tetrahydrofuran-3-yl)-1,2,3,4-tetrahydro-1,8-naphthyridine

Procedure

The title compound was synthesized in an analogous manner to intermediate 312, by replacing 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1, 3,2-dioxaborolane with 2-(2,5-dihydrofuran-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The title compound was obtained as a viscous, turbid light yellow oil. (UPLC-MS 3) tR 0.50 min; ESI-MS 279.2 [M+H]+.

Sources & evidence

ORD record
ord-c0977462fdef426aa747d4b3bbcb81fc
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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