4-Bromopyridazine → HCID 25115595, compound

HRID 1099414Notes

Reaction equation

[CH2:1]([N:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2B2OC(C)(C)C(C)(C)O2)[O:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:36]1[CH:41]=[CH:40][N:39]=[N:38][CH:37]=1>>[CH2:1]([N:8]([CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[C:36]2[CH:41]=[CH:40][N:39]=[N:38][CH:37]=2)[O:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 178889274-Bromopyridazine

HCID 25114260(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine

Product 1

HCID 25115595HCID 25115595, compoundYield 62%

Procedure

The title compound was synthesized as described for Intermediate example I-48 in 62% yield starting from (3S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl)chroman-3-amine and 4-bromopyridazine (1.2 equiv). The reaction was irradiated in microwave at 140° C. for 45 min: 1H NMR (400 MHz, CDCl3) δ ppm 9.26 (dd, 1 H), 9.19-9.22 (m, 1 H), 7.38 (dd, 1 H), 7.26-7.34 (m, 8 H), 7.16-7.25 (m, 3 H), 6.91 (d, 1 H), 6.78 (dd, 1 H), 4.36-4.43 (m, 1 H), 4.06 (t, 1 H), 3.64-3.77 (m, 4 H), 3.15-3.25 (m, 1 H), 2.86 (dd, 1 H), 2.57 (ddd, 1 H); MS (ESI) m/z 408[M+H+].

Workup

customThe reaction was irradiated in microwave at 140° C. for 45 min

Sources & evidence

ORD record: ord-ef301528b46649b8a11336bafe70b39c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143408B2

Reaction notes

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