4-Bromopyridazine → (2R)-N,N-dibenzyl-8-pyridazin-4-yl-1,2,3,4-tetrahydronaphthalen-2-amine

HRID 1099420Notes

Reaction equation

HRID 1099420 reaction equation
[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@H:9]1[CH2:18][C:17]2[C:16](B(O)O)=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:30]1[CH:35]=[CH:34][N:33]=[N:32][CH:31]=1>>[CH2:1]([N:8]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C@@H:9]1[CH2:10][CH2:11][C:12]2[C:17](=[C:16]([C:30]3[CH:35]=[CH:34][N:33]=[N:32][CH:31]=3)[CH:15]=[CH:14][CH:13]=2)[CH2:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 178889274-BromopyridazineHCID 59354908[(7R)-7-(dibenzylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]boronic acid

Product 1

HCID 25116057(2R)-N,N-dibenzyl-8-pyridazin-4-yl-1,2,3,4-tetrahydronaphthalen-2-amineYield 45%

Procedure

The title compound was synthesized as described for Intermediate example I-48 in 45% yield starting from [(7R)-7-(dibenzylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]boronic acid and 4-bromopyridazine (1 equiv): 1H NMR (400 MHz, CDCl3) δ ppm 9.24 (dd, 1 H), 9.17 (dd, 1 H), 7.31-7.36 (m, 5 H), 7.25-7.30 (m, 4 H), 7.15-7.24 (m, 4 H), 7.00 (dd, 1 H), 3.59-3.70 (m, 4 H), 2.92-3.08 (m, 2 H), 2.69-2.89 (m, 2 H), 2.51-2.62 (m, 1 H), 2.13-2.25 (m, 1 H), 1.71-1.86 (m, 1 H); MS (ESI) m/z 406[M+H+].

Sources & evidence

ORD record
ord-a0c2f858795a4bc091279be154d4cf0d
Source dataset
uspto-grants-2012_03
Patent number
US08143408B2

Reaction notes

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