2-Benzyloxy-6-bromopyridine → 6-(benzyloxy)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridin-2-amine

HRID 1697953Notes

Reaction equation

HRID 1697953 reaction equation
CC(C)([O-])C.[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.[CH3:35][C:36]1([CH3:50])[C:40]([CH3:42])([CH3:41])[O:39][B:38]([C:43]2[CH:49]=[CH:48][C:46]([NH2:47])=[CH:45][CH:44]=2)[O:37]1.Br[C:52]1[CH:57]=[CH:56][CH:55]=[C:54]([O:58][CH2:59][C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)[N:53]=1>C(O)(C)(C)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH2:59]([O:58][C:54]1[N:53]=[C:52]([NH:47][C:46]2[CH:48]=[CH:49][C:43]([B:38]3[O:37][C:36]([CH3:50])([CH3:35])[C:40]([CH3:41])([CH3:42])[O:39]3)=[CH:44][CH:45]=2)[CH:57]=[CH:56][CH:55]=1)[C:60]1[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=1

Participants

7

Reactant 4

HCID 8174752-Benzyloxy-6-bromopyridineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 23676156Sodium t-butoxide

Product 1

HCID 582225306-(benzyloxy)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyridin-2-amineYield 65%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 6386tert-ButanolSolvent

Procedure

Sodium tert-butoxide (556 mg, 5.78 mmol), 2-Dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (98 mg, 0.25 mmol), Bis(dibenzylideneacetone)palladium(0) (96 mg, 0.17 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (ou) (1.00 g, 4.57 mmol) and 2-Bromo-6-benzyloxypyridine (ot) (1.10 g, 4.15 mmol) were mixed in tert-Butyl alcohol (20 mL), which was purged by nitrogen for a few minutes. The dark orange mixture was microwaved at 120° C. for 15 minutes, and the reaction was quenched by 10% citric acid (aqueous). After purification on silica gel column, the desired product ow (1.08 g 65% yield) was obtained as slightly brown solid: 1H NMR (400 MHz, CDCl3) δ 7.75 (d, J=8.4 Hz, 2H), 7.49-7.41 (m, 3H), 7.41-7.34 (m, 4H), 7.34-7.27 (m, 1H), 6.46 (s, 1H), 6.44 (d, J=7.9 Hz, 1H), 6.30 (d, J=7.9 Hz, 1H), 5.37 (s, 2H), 1.34 (s, 12H); LC-MS m/z=403 (M+H).

Workup

  1. customwhich was purged by nitrogen for a few minutes
  2. customThe dark orange mixture was microwaved at 120° C. for 15 minutes
  3. customthe reaction was quenched by 10% citric acid (aqueous)
  4. customAfter purification on silica gel column

Sources & evidence

ORD record
ord-043eb544093e4f818214d04dbc94384e
Source dataset
uspto-grants-2012_04
Patent number
US08163763B2

Reaction notes

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