1-Bromo-3-methylbutane → HCID 46195712, compound

HRID 1407661Notes

Reaction equation

HRID 1407661 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]3[C:11]4([CH2:21][O:22][C:8]3=[CH:7][C:5]=2[N:6]=1)[C:19]1[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:13][C:12]4=[O:20].Br[CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27].BrCC1CCCCO1.N1C2C(=CC=CC=2)C2(C3=CC4SC=NC=4C=C3OC2)C1=O>>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]3[C:11]4([CH2:21][O:22][C:8]3=[CH:7][C:5]=2[N:6]=1)[C:19]1[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=1)[N:13]([CH2:24][CH2:25][CH:26]([CH3:28])[CH3:27])[C:12]4=[O:20]

Participants

5

Reactant 4

HCID 78911-Bromo-3-methylbutaneHCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 461958502-methylspiro[furo[2,3-f][1,3]benzothiazole-7,3'-indol]-2'(1'H)-oneHCID 86697476HCID 86697476, compound

Product 1

HCID 46195712HCID 46195712, compound

Procedure

Following the procedure as described in EXAMPLE 4 and making non-critical variations using 2-methylspiro[furo[2,3-f][1,3]benzothiazole-7,3′-indol]-2′(1′H)-one to replace 5,6-dihydrospiro[benzo[1,2-b:5,4-b′]difuran-3,3′-indol]-2″(1′H)-one, and 1-bromo-3-methylbutane to replace 2-(bromomethyl)tetrahydro-2H-pyran, methylbutyl)spiro[furo[2,3-f][1,3]benzothiazole-7,3′-indol]-2′(1′H)-one was obtained (71%) as a colorless solid: mp 137-138° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ7.60 (d, J=8.6 Hz, 1H), 7.32-7.27 (m, 1H), 7.13-7.08 (m, 1H), 7.03-6.92 (m, 3H), 5.03 (d, J=8.8 Hz, 1H), 4.78 (d, J=8.8 Hz, 1H), 4.12-4.01 (m, 1H), 3.71-3.60 (m, 1H), 2.56 (s, 3H), 1.93-1.61 (m, 3H), 1.06-1.00 (m, 6H); 13C NMR (75 MHz, CDCl3) δ176.8, 169.3, 160.4, 149.4, 142.8, 132.9, 129.1, 128.7, 123.6, 122.8, 122.2, 120.4, 108.6, 108.4, 81.1, 58.2, 39.2, 36.1, 26.0, 23.0, 22.5, 20.3; MS (ES+) m/z 378.5 (M+1).

Workup

  1. customwas obtained (71%) as a colorless solid

Sources & evidence

ORD record
ord-c7cbd11c96b44205bed9adfc19198a7f
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

Loading…