4-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride) → HCID 70683112, compound

HRID 1054058Notes

Reaction equation

HRID 1054058 reaction equation
[C:1]1([N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:8]2[CH:13]=[CH:12][C:11](B(O)O)=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:23]1([CH2:28][C:29]2[CH:30]=[CH:31][C:32](Br)=[N:33][CH:34]=2)[CH:27]=[CH:26][N:25]=[CH:24]1>>[N:23]1([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:11]3[CH:12]=[CH:13][C:8]([N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:9][CH:10]=3)=[N:33][CH:34]=2)[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

3

Reactant 2

HCID 121669344-(Diphenylamino)phenylboronic Acid (contains varying amounts of Anhydride)HCID 70680985HCID 70680985, compound

Product 1

HCID 70683112HCID 70683112, compound

Procedure

Synthesized using 4-(diphenylamino)phenylboronic acid (364 mg, 1.26 mmol) and 1a (150 mg, 0.63 mmol) according to Method C. Yellow solid. Yield: 140 mg, 0.34 mmol, 55%. 1H NMR (500 MHz, CDCl3): δH (ppm): 5.16, (s, 2H), 6.93 (t, J=1.3 Hz, 1H), 7.06 (tt, J=7.3, 1.3 Hz, 2H), 7.12-7.15 (m, 7H), 7.25-7.29 (m, 4H), 7.45 (dd, J=8.2, 2.2 Hz, 1H), 7.58 (br, s, 1H), 7.65 (dd, J=8.2, 0.6 Hz, 1H), 7.83-7.86 (m, 2H), 8.54 (dd, J=2.5, 0.6 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=48.2, 119.0, 119.8, 122.8, 123.4, 124.9, 127.7, 129.2, 129.3, 130.2, 132.0, 135.7, 137.3, 147.3, 148.5, 149.1, 157.3; MS (ESI): m/z=402.94 [M+H]+.

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-4367d05e34854a669f1842a06f99e2c6
Source dataset
uspto-grants-2016_07
Patent number
US09394290B2

Reaction notes

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