Chloroacetonitrile → HCID 59352512, compound

HRID 422845Notes

Reaction equation

Cl[CH2:2][C:3]#[N:4].BrCC1C=CC=C(C#N)C=1.[NH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]2([C:27]3=[CH:28][C:29]4[O:33][CH2:32][O:31][C:30]=4[CH:34]=[C:26]3[O:25][CH2:24]2)[C:16]1=[O:35]>>[O:35]=[C:16]1[C:17]2([C:27]3=[CH:28][C:29]4[O:33][CH2:32][O:31][C:30]=4[CH:34]=[C:26]3[O:25][CH2:24]2)[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:15]1[CH2:2][C:3]#[N:4]

Participants

Reactant 3

HCID 7856Chloroacetonitrile

HCID 97249Benzonitrile, 3-(bromomethyl)-

HCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Product 1

HCID 59352512HCID 59352512, compound

Procedure

Following the procedure as described in PREPARATION 7 and making non-critical variations using chloroacetonitrile to replace α-bromo-m-tolunitrile, and spiro[furo[2,3-f][1,3]benzodioxole-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, (2′-oxospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-1′(2′H)-yl)acetonitrile was obtained (61%) as a colorless solid: mp 170-172° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.38 (dt, J=7.7, 1.2 Hz, 1H), 7.26 (d, J=7.7 Hz, 1H), 7.20 (d, J=7.3 Hz, 1H), 7.11 (dt, J=7.7, 1.1 Hz, 1H), 6.66 (s, 1H), 6.21 (s, 1H), 5.89 (d, J=1.5 Hz, 2H), 4.94 (ABq, 2H), 4.73 (ABq, 2H); 13C NMR (75 MHz, DMSO-d6) δ 176.8, 155.8, 148.9, 142.2, 141.0, 131.9, 129.4, 124.3, 124.3, 119.8, 116.0, 109.7, 103.5, 101.9, 93.8, 80.1, 57.8, 28.8; MS (ES+) m/z 321.3 (M+1).

Workup

customas described in PREPARATION 7

Sources & evidence

ORD record: ord-6c1cec1fa0d547668e44fd84fd90526e
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101647B2

Reaction notes

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