N-[(1,2-dimethylindol-3-yl)methylidene]hydroxylamine → HCID 11223337, compound
Reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[CH:6][C:5]=1[Br:12].[CH3:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([CH:24]=[N:25][OH:26])=[C:16]1[CH3:27]>>[Br:12][C:5]1[CH:6]=[C:7]([CH2:10][O:26]/[N:25]=[CH:24]/[C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]([CH3:14])[C:16]=2[CH3:27])[CH:8]=[CH:9][C:4]=1[C:3]([OH:2])=[O:13]Participants
Procedure
This compound was produced using similar methods as that used in Step 4, example 6, starting with 2-bromo-4-bromomethyl-benzoic acid methyl ester (0.28 g, 0.91 mmol) and 1,2-dimethyl-1H-indole-3-carbaldehyde oxime (0.18 g, 0.96 mmol). The crude material was purified by flash chromatography through silica gel using ethyl acetate/hexanes (50/50 with 1% formic acid) followed by HPLC (65% acetonitrile in 0.1% trifluoroacetic acid solution) and one final recrystallization from ethyl acetate/hexanes to give 2-bromo-4-[({[(1E)-(1,2-dimethyl-1H-indol-3-yl)methylidene]amino}oxy)methyl]benzoic acid (0.16 g, 45%) as a white solid. mp=165-166° C. 1H NMR (400 MHz, DMSO-d6); δ 13.34 (bs, 1H), 8.53 (s, 1H), 7.88 (d, 1H), 7.78 (s, 1H), 7.75 (d, 1H), 7.51 (d, 1H), 7.44 (d, 1H), 7.16 (t, 1H), 7.08 (t, 1H), 5.17 (s, 2H), 3.67 (s, 3H), 2.47 (s, 3H). Mass spec; (ES+) m/z 401.1, (ES−) m/z 399.0. Elemental analysis; Calculated for C19H17BrN2O3: C, 56.87; H, 4.27; N, 6.98. Found: C, 56.84; H, 4.3; N, 6.92.
Workup
- customThis compound was produced
- customThe crude material was purified by flash chromatography through silica gel
- customrecrystallization from ethyl acetate/hexanes
Sources & evidence
- ORD record
- ord-d188fb24d12d4894be26b24af782d411
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07342039B2
Reaction notes
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