1,3-Dibromopropane → HCID 76310296, compound

HRID 925118Notes

Reaction equation

HRID 925118 reaction equation
Br[CH2:2][CH2:3][CH2:4]Br.BrCCC(Br)CC.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][C:22]#[N:23])[CH:18]=[CH:19][CH:20]=1.COC1C=C(CC#[N:36])C=CC=1OC>>[CH3:13][O:14][C:15]1[CH:16]=[C:17]2[C:18](=[CH:19][CH:20]=1)[N:23]=[C:22]([NH2:36])[C:21]12[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 80011,3-DibromopropaneHCID 667273,4-DimethoxybenzeneacetonitrileHCID 88310(3-Methoxyphenyl)acetonitrileHCID 1426061,3-Dibromopentane

Product 1

HCID 76310296HCID 76310296, compound

Procedure

5′-Methoxyspiro[cyclobutane-1,3′-indol]-2′-amine was prepared according to the procedure outlined in Example 2 substituting 1,3-dibromopropane for 1,3-dibromopentane and 2-(3-methoxyphenyl)acetonitrile for 2-(3,4-dimethoxyphenyl)acetonitrile in Step 1 of the three-step sequence. 1H NMR (400 MHz, DMSO) δ 11.87 (s, 1H), 10.02 (s, 1H), 9.83 (s, 1H), 7.42 (d, J=2.4 Hz, 1H), 7.05 (d, J=8.5 Hz, 1H), 6.89 (dd, J=8.6, 2.5 Hz, 1H), 3.80 (s, 3H), 2.40-2.24 (m, 1H), 2.24-2.04 (m, 3H). MS (APCI) m/z 203 (M+H)+.

Sources & evidence

ORD record
ord-b2eb0e10d6f9490eaeb5afe120d1f759
Source dataset
uspto-grants-2016_03
Patent number
US09284272B2

Reaction notes

Loading…