2-Bromo-1-indanone → HCID 178495752, compound

HRID 1469961Notes

Reaction equation

HRID 1469961 reaction equation
Br[CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.[CH2:12]1[CH:19]2[C:15]3([C:21]([NH:23][C:24]([NH:26][CH2:27][CH2:28][O:29][CH3:30])=[S:25])=[O:22])[CH2:16][CH:17]([CH2:20][CH:13]1[CH2:14]3)[CH2:18]2>>[CH3:30][O:29][CH2:28][CH2:27][N:26]1[C:3]2[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[CH2:10][C:2]=2[S:25]/[C:24]/1=[N:23]\[C:21]([C:15]12[CH2:16][CH:17]3[CH2:20][CH:13]([CH2:12][CH:19]1[CH2:18]3)[CH2:14]2)=[O:22]

Participants

3

Reactant 2

HCID 1372032-Bromo-1-indanoneHCID 866524581-(Hexahydro-2,5-methano-pentalene-3a-carbonyl)-3-(2-methoxyethyl)-thiourea

Product 1

HCID 178495752HCID 178495752, compound

Procedure

Commercially available 2-bromo-indan-1-one and the product of Example 14B were processed according to the method of Example 14C to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.55-1.70 (m, 4H), 1.70-1.86 (m, 4H), 2.09-2.20 (m, J=9.0, 2.5 Hz, 2H), 2.24-2.34 (m, 2H), 2.60 (t, J=6.6 Hz, 1H), 3.23 (s, 3H), 3.74-3.86 (m, 4H), 4.69 (t, J=5.4 Hz, 2H), 7.29 (td, J=7.4, 0.8 Hz, 1H), 7.39 (td, 1H), 7.58 (d, J=7.1 Hz, 1H), 7.74 (d, J=7.8 Hz, 1H); MS (ESI+) m/z 395 (M+H)+; Anal. Calculated for C23H26N2O2S: C, 70.02; H, 6.64; N, 7.10. Found: C, 69.83; H, 6.57; N, 6.92.

Sources & evidence

ORD record
ord-80bce317c36942d59ca3b4b0f40347c0
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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