1-Bromopentane → HCID 68600771, compound

HRID 2385332Notes

Reaction equation

HRID 2385332 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:21]3[C:12](=[CH:13][C:14]4[O:19][CH2:18][CH2:17][O:16][C:15]=4[CH:20]=3)[O:11][CH2:10]2)[C:2]1=O.N1C2C(=CC=CC=2)[C@@]2(C3C(=CC4OCCOC=4C=3)[O:33]C2)C1=O.Cl[CH2:46][C:47]1[CH:48]=[C:49]([S:53]([N:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)(=[O:55])=[O:54])[CH:50]=[CH:51][CH:52]=1.BrCCCCC>>[N:56]1([S:53]([C:49]2[CH:48]=[C:47]([CH:52]=[CH:51][CH:50]=2)[CH2:46][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]3([C:21]4[C:12](=[CH:13][C:14]5[O:19][CH2:18][C:17](=[O:33])[O:16][C:15]=5[CH:20]=4)[O:11][CH2:10]3)[CH2:2]2)(=[O:55])=[O:54])[CH2:61][CH2:60][O:59][CH2:58][CH2:57]1

Participants

5

Reactant 4

HCID 80571-BromopentaneHCID 21609954-[[3-(Chloromethyl)phenyl]sulfonyl]morpholineHCID 58224164Spiro[furo[2,3-g]-1,4-benzodioxin-8(7H),3'-[3H]indol]-2'(1'H)-one, 2,3-dihydroHCID 59352191Spiro[furo[2,3-g]-1,4-benzodioxin-8(7H),3'-[3H]indol]-2'(1'H)-one, 2,3-dihydro-, (3'S)-

Product 1

HCID 68600771HCID 68600771, compound

Procedure

Following the procedure as described in EXAMPLE 7.3 and making non-critical variations using 2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace (S)-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one, and 4-(3-(chloromethyl)phenylsulfonyl)morpholine to replace 1-bromopentane, 1′-[3-(morpholin-4-ylsulfonyl)benzyl]-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2(1′H)-one was obtained (40%) as a colorless solid: 1H NMR (300 MHz, DMSO-d6) δ 7.73-7.64 (m, 4H), 7.29-7.18 (m, 2H), 7.05 (dd, J=7.3, 5.6 Hz, 2H), 6.52 (s, 1H), 6.11 (s, 1H), 5.09 (ABq, 2H), 4.74 (dd, J=9.3 Hz, 2H), 4.04-4.21 (m, 4H), 3.56 (t, J=4.5 Hz, 4H), 2.84-2.65 (m, 4H); 13C NMR (75 MHz, DMSO-d6) δ 176.9, 154.8, 144.2, 141.9, 138.0, 137.9, 134.7, 132.2, 131.6, 130.1, 128.8, 126.7, 125.9, 123.9, 123.3, 121.0, 110.9, 109.5, 98.9, 79.5, 65.2, 64.2, 63.6, 57.3, 45.8, 42.5; MS (ES+) m/z 534.9 (M+1).

Sources & evidence

ORD record
ord-810cc05feff84757b2c13780eb3a6940
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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