8-Bromo-2H-benzo[b][1,4]thiazin-3(4H)-one → 8-Bromo-3,4-dihydro-2H-benzo[B][1,4]thiazine

Reaction equation

BrC1C2C1CNC1C=CC=CC=12.BrC1C2C3CC3C(=O)NC=2C=CC=1.[Br:26][C:27]1[C:32]2[S:33][CH2:34][C:35](=O)[NH:36][C:31]=2[CH:30]=[CH:29][CH:28]=1>>[Br:26][C:27]1[C:32]2[S:33][CH2:34][CH2:35][NH:36][C:31]=2[CH:30]=[CH:29][CH:28]=1

Participants

Reactant 3

HCID 717427308-Bromo-2H-benzo[b][1,4]thiazin-3(4H)-one

HCID 717427347-Bromo-3,7B-dihydro-1H-cyclopropa[C]quinolin-2(1AH)-one

HCID 86712576bromo-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline

Product 1

HCID 717427318-Bromo-3,4-dihydro-2H-benzo[B][1,4]thiazine

Procedure

The title compound was prepared using a procedure analogous to bromo-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline except that 7-bromo-3,7b-dihydro-1H-cyclopropa[c]quinolin-2(1aH)-one was replaced with 8-bromo-2H-benzo[b][1,4]thiazin-3(4H)-one. LCMS, [M+H]+=231.9. 1H NMR (400 MHz, MeOD) δ 6.86-6.80 (m, 1H), 6.73 (t, J=7.9 Hz, 1H), 6.52 (dd, J=8.1, 1.3 Hz, 1H), 3.56-3.49 (m, 2H), 3.09-3.01 (m, 2H).

Sources & evidence

ORD record: ord-78bf23f88cd34ef88eb1ef72d87051e6
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062028B2

Reaction notes

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