4-(1-Benzyloxy-ethyl)-5-bromo-nicotinonitrile → 4-(1-Benzyloxy-ethyl)-5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-nicotinonitrile

HRID 712708Notes

Reaction equation

HRID 712708 reaction equation
[CH2:1]([O:8][CH:9]([C:11]1[C:16]([C:17]#[N:18])=[CH:15][N:14]=[CH:13][C:12]=1Br)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]3[C:35](=[N:36][CH:37]=2)[NH:34][CH2:33][CH2:32][CH2:31]3)O1>>[CH2:1]([O:8][CH:9]([C:11]1[C:16]([C:17]#[N:18])=[CH:15][N:14]=[CH:13][C:12]=1[C:32]1[CH:33]=[N:34][C:35]2[NH:36][CH2:37][CH2:28][CH2:29][C:30]=2[CH:31]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1176674244-(1-Benzyloxy-ethyl)-5-bromo-nicotinonitrileHCID 1189899286-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydro-1,8-naphthyridine

Product 1

HCID 1176674554-(1-Benzyloxy-ethyl)-5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-nicotinonitrile

Procedure

4-(1-Benzyloxy-ethyl)-5-(5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-nicotinonitrile is synthesized according to the procedure of Suzuki Coupling Method VI using 4-(1-benzyloxy-ethyl)-5-bromo-nicotinonitrile and crude 6-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydro-[1,8]naphthyridine (which is prepared according to Step 4 of Example 105).

Sources & evidence

ORD record
ord-7be99ff27704400d9829bbc42b27c5e6
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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